azelaic acid
1,7-heptanedicarboxylic acid
 
Notes:
Occurs in rancid fats. Isol. from a few higher plants Azelaic acid (AZA) is a naturally occurring saturated nine-carbon dicarboxylic acid (COOH (CH2)7-COOH). It possesses a variety of biological actions both in vitro and in vivo. Interest in the biological activity of AZA arose originally out of studies of skin surface lipids and the pathogenesis of hypochromia in pityriasis versicolor infection. Later, it was shown that Pityrosporum can oxidize unsaturated fatty acids to C8-C12 dicarboxylic acids that are cornpetitive inhibitors of tyrosinase in vitro. Azelaic acid was chosen for further investigation and development of a new topical drug for treating hyperpigmentary disorders for the following reasons: it possesses a middle-range of antityrosinase activity, is inexpensive, and more soluble to be incorporated into a base cream than other dicarboxylic acids. Azelaic acid is another option for the topical treatment of mild to moderate inflammatory acne vulgaris. It offers effectiveness similar to that of other agents without the systemic side effects of oral antibiotics or the allergic sensitization of topical benzoyl peroxide and with less irritation than tretinoin. Azelaic acid is less expensive than certain other prescription acne preparations, but it is much more expensive than nonprescription benzoyl peroxide preparations. Whether it is safe and effective when used in combination with other agents is not known. (PMID: 7737781, 8961845); Azelaic acid is a saturated dicarboxylic acid found naturally in wheat, rye, and barley. It is a natural substance that is produced by Malassezia furfur (also known as Pityrosporum ovale), a yeast that lives on normal skin. It is effective against a number of skin conditions, such as mild to moderate acne, when applied topically in a cream formulation of 20%. It works in part by stopping the growth of skin bacteria that cause acne, and by keeping skin pores clear. Azelaic acid's antimicrobial action may be attributable to inhibition of microbial cellular protein synthesis.; Azelaic acid is a saturated dicarboxylic acid found naturally in wheat, rye, and barley. It is a natural substance that is produced by Malassezia furfur (also known as Pityrosporum ovale), a yeast that lives on normal skin. It is effective against a number of skin conditions, such as mild to moderate acne, when applied topically in a cream formulation of 20%. Azelaic acid may be useful as a hair growth stimulant.[citation needed]
  • Charkit Chemical
    • Charkit Chemical Corporation
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    • Penta International Corporation
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      Product(s):
      01-42700 AZELAIC ACID 90%
      01-42710 AZELAIC ACID 98%
       
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nonanedioic acid (Click)
CAS Number: 123-99-9Picture of molecule
ECHA EINECS - REACH Pre-Reg: 204-669-1
FDA UNII: F2VW3D43YT
Nikkaji Web: J10.058G
Beilstein Number: 1101094
MDL: MFCD00004432
CoE Number: 10079
XlogP3: 1.60 (est)
Molecular Weight: 188.22332000
Formula: C9 H16 O4
BioActivity Summary: listing
NMR Predictor: Predict (works with chrome or firefox)
Category: indirect food additives: adhesives and components of coatings
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar: Search
Google Books: Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Perfumer and Flavorist: Search
Google Patents: Search
US Patents: Search
EU Patents: Search
IBM Patents: Obtain
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Pubchem Patents: Search
PubMed: Search
NCBI: Search
Flavis Number: 08.103 (Old)
DG SANTE Food Flavourings: 08.103  nonanedioic acid
DG SANTE Food Contact Materials: nonanedioic acid
FDA Mainterm: Azelaic acid
FDA Regulation:
FDA PART 175 -- INDIRECT FOOD ADDITIVES: ADHESIVES AND COMPONENTS OF COATINGS
Subpart B--Substances for Use Only as Components of Adhesives
Sec. 175.105 Adhesives.
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Melting Point: 106.00 to  107.00 °C. @ 760.00 mm Hg
Boiling Point: 356.00 to  357.00 °C. @ 760.00 mm Hg
Boiling Point: 228.00 to  229.00 °C. @ 10.00 mm Hg
Vapor Density: 6.5 ( Air = 1 )
Flash Point: 419.00 °F. TCC ( 215.00 °C. )
logP (o/w): 1.570
Soluble in:
 alcohol
 water, 2400 mg/L @ 20 °C (exp)
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Organoleptic Properties:
  
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Cosmetic Information:
CosIng: cosmetic data
Cosmetic Uses: buffering agents
masking agents
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Suppliers:
Charkit Chemical
AZELAIC ACID
Oleo Solutions
Emerox 1110
Odor: characteristic
Use: Adhesives and Lubricants, Industrial, Inks and Coatings
Oleo Solutions
Emerox 1112
Odor: characteristic
Use: Adhesives and Lubricants, Industrial, Inks and Coatings
Oleo Solutions
Emerox 1144
Odor: characteristic
Use: Adhesives and Lubricants, Industrial, Inks and Coatings
Oleo Solutions
Emerox 1185
Odor: characteristic
Use: Adhesives and Lubricants, Industrial, Inks and Coatings
Penta International
AZELAIC ACID 90%
Penta International
AZELAIC ACID 98%
Santa Cruz Biotechnology
For experimental / research use only.
Azelaic Acid
Sigma-Aldrich: Aldrich
For experimental / research use only.
Azelaic acid 98%
TCI AMERICA
For experimental / research use only.
Azelaic Acid >85.0%(GC)
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Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
gavage-rat LD50  [sex: M,F] > 4000 mg/kg
(Mingrone et al., 1983)

gavage-rabbit LD50  [sex: M,F] > 4000 mg/kg
(Mingrone et al., 1983)

oral-rat LD50  > 5000 mg/kg
National Technical Information Service. Vol. AD-A067-313

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: indirect food additives: adhesives and components of coatings
Recommendation for azelaic acid usage levels up to:
 not for fragrance use.
 
Maximised Survey-derived Daily Intakes (MSDI-EU): 0.0012 (μg/capita/day)
Modified Theoretical Added Maximum Daily Intake (mTAMDI): 3200 (μg/person/day)
Threshold of Concern:1800 (μg/person/day)
Structure Class: I
 
Food categories according to Commission Regulation EC No. 1565/2000 (EC, 2000) in FGE.06 (EFSA, 2002a). According to the Industry the "normal" use is defined as the average of reported usages and "maximum use" is defined as the 95th percentile of reported usages (EFSA, 2002i).
Note: mg/kg = 0.001/1000 = 0.000001 = 1/1000000 = ppm.
 average usage mg/kgmaximum usage mg/kg
Dairy products, excluding products of category 02.0 (01.0): 3.0000015.00000
Fats and oils, and fat emulsions (type water-in-oil) (02.0): 2.0000010.00000
Edible ices, including sherbet and sorbet (03.0): 3.0000015.00000
Processed fruit (04.1): 2.0000010.00000
Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2): --
Confectionery (05.0): 10.0000050.00000
Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0): 5.0000025.00000
Bakery wares (07.0): 10.0000050.00000
Meat and meat products, including poultry and game (08.0): 2.0000010.00000
Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0): 2.0000010.00000
Eggs and egg products (10.0): --
Sweeteners, including honey (11.0): --
Salts, spices, soups, sauces, salads, protein products, etc. (12.0): 5.0000025.00000
Foodstuffs intended for particular nutritional uses (13.0): 10.0000050.00000
Non-alcoholic ("soft") beverages, excl. dairy products (14.1): 3.0000015.00000
Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2): 10.0000050.00000
Ready-to-eat savouries (15.0): 15.0000075.00000
Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0): 5.0000025.00000
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Safety References:
European Food Safety Athority(efsa): Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...
European Food Safety Authority (EFSA) reference(s):
Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC) on a request from the Commission related to - Flavouring Group Evaluation 10: Aliphatic primary and secondary saturated and unsaturated alcohols, aldehydes, acetals, carboxylic acids and esters containing an additional oxygenated functional group and lactones from chemical groups 9, 13 and 30 - (Commission Regulation (EC) No 1565/2000 of 18 July 2000)
View page or View pdf
Flavouring Group Evaluation 10, Revision 1 (FGE10 Rev1)[1] - Aliphatic primary and secondary saturated and unsaturated alcohols, aldehydes, acetals, carboxylic acids and esters containing an additional oxygenated functional group and lactones from chemical groups 9, 13 and 30 - Scientific Opinion of the Panel on Food Additives, Flavourings, Processing Aids and Materials in Contact with Food (AFC)
View page or View pdf
Flavouring Group Evaluation 64 (FGE.64): Consideration of aliphatic acyclic diols, triols, and related substances evaluated by JECFA (57th meeting) structurally related to aliphatic primary and secondary saturated and unsaturated alcohols, aldehydes, acetals, carboxylic acids and esters containing an additional oxygenated functional group and lactones from chemical groups 9, 13 and 30 evaluated by EFSA in FGE.10Rev1 (EFSA, 2008ab)
View page or View pdf
Scientific Opinion on Flavouring Group Evaluation 92 (FGE.92): Consideration of aliphatic acyclic diols, triols, and related substances evaluated by JECFA (68th meeting) structurally related to aliphatic primary and secondary saturated and unsaturated alcohols, aldehydes, acetals, carboxylic acids and esters containing an additional oxygenated functional group and lactones evaluated by EFSA in FGE.10Rev1 (2009)
View page or View pdf
Scientific Opinion on Flavouring Group Evaluation 10, Revision 2 (FGE.10Rev2): Aliphatic primary and secondary saturated and unsaturated alcohols, aldehydes, acetals, carboxylic acids and esters containing an additional oxygenated functional group and lactones from chemical groups 9, 13 and 30
View page or View pdf
Scientific Opinion on Flavouring Group Evaluation 10, Revision 3 (FGE.10Rev3): Aliphatic primary and secondary saturated and unsaturated alcohols, aldehydes, acetals, carboxylic acids and esters containing an additional oxygenated functional group and lactones from chemical groups 9, 13 and 30
View page or View pdf
EPI System: View
ClinicalTrials.gov: search
Daily Med: search
NLM Hazardous Substances Data Bank: Search
AIDS Citations: Search
Cancer Citations: Search
Toxicology Citations: Search
Env. Mutagen Info. Center: Search
NLM Developmental and Reproductive Toxicity: Search
EPA Substance Registry Services (TSCA): 123-99-9
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 2266
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 1
 nonanedioic acid
Chemidplus: 0000123999
RTECS: CM1980000 for cas# 123-99-9
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References:
 nonanedioic acid
NIST Chemistry WebBook: Search Inchi
Canada Domestic Sub. List: 123-99-9
Pubchem (cid): 2266
Pubchem (sid): 134974895
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Other Information:
(IUPAC): Atomic Weights of the Elements 2009
(IUPAC): Atomic Weights of the Elements 2009 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
FDA Everything Added to Food in the United States (EAFUS): View
CHEBI: View
CHEMBL: View
Golm Metabolome Database: Search
KEGG (GenomeNet): C08261
HMDB (The Human Metabolome Database): HMDB00784
FooDB: FDB012192
Export Tariff Code: 2917.13.0000
MedlinePlusSupp: View
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
RSC Learn Chemistry: View
Formulations/Preparations:
topical: cream: 20% azelex (with propylene glycol) (allergan), finevin (with propylene glycol) (berlex). gel: 15% finacea (with propylene glycol) (berlex).
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
 buffering agents 
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Occurrence (nature, food, other): note
 bean black bean root
Search Trop  Picture
 bean field bean root
Search Trop  Picture
 beer - up to1.5 mg/kg
Search  Picture
 potato leaf
Search Trop  Picture
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Synonyms:
 anchoic acid
 azalaic acid
 azelaicacid
 azelainic acid
 emerox 1110
 finacea
1,7-heptane dicarboxylic acid
 heptanedicarboxylic acid
1,7-heptanedicarboxylic acid
 lepargylic acid
 nonane dioic acid
1,9-nonane dioic acid
 nonanedioic acid
1,9-nonanedioic acid
N-nonanedioic acid
 nonanedioicacid
 skinorem
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Articles:
PubMed: Modification of wheat starch with succinic acid/acetanhydride and azelaic acid/acetanhydride mixtures. II. Chemical and physical properties.
J-Stage: Cellulase Applied to the Leaves of Sweet Pepper (Capsicum annuum L. var. grossum) Upregulates the Production of Salicylic and Azelaic Acids
PubMed: Efficacy of azelaic acid on hepatic key enzymes of carbohydrate metabolism in high fat diet induced type 2 diabetic mice.
PubMed: UPLC-QTOF/MS metabolic profiling unveils urinary changes in humans after a whole grain rye versus refined wheat bread intervention.
PubMed: Effect of ionization and vehicle on skin absorption and penetration of azelaic acid.
PubMed: Azelaic acid gel 15% in the management of papulopustular rosacea: a status report on available efficacy data and clinical application.
PubMed: Acne vulgaris.
PubMed: Alternative therapies for common dermatologic disorders, part 1.
PubMed: A review of the diagnosis and treatment of rosacea.
PubMed: Phenolic and short-chained aliphatic organic acid constituents of wild oat (Avena fatua L.) seeds.
PubMed: Rosacea: a review of current topical, systemic and light-based therapies.
PubMed: Acne vulgaris.
PubMed: Cumulative irritation potential among metronidazole gel 1%, metronidazole gel 0.75%, and azelaic acid gel 15%.
PubMed: The use of topical azelaic acid for common skin disorders other than inflammatory rosacea.
PubMed: Immunochemical detection of a novel lysine adduct using an antibody to linoleic acid hydroperoxide-modified protein.
PubMed: New treatments and therapeutic strategies for acne.
PubMed: Melasma. Etiologic and therapeutic considerations.
PubMed: Preliminary studies of a dicarboxylic acid as an energy substrate in man.
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